CN105399787A - Method for extracting hesperidin, neohesperidin and synephrine from citrus peel and citrus fruits - Google Patents
Method for extracting hesperidin, neohesperidin and synephrine from citrus peel and citrus fruits Download PDFInfo
- Publication number
- CN105399787A CN105399787A CN201510892989.6A CN201510892989A CN105399787A CN 105399787 A CN105399787 A CN 105399787A CN 201510892989 A CN201510892989 A CN 201510892989A CN 105399787 A CN105399787 A CN 105399787A
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- CN
- China
- Prior art keywords
- synephrine
- neohesperidin
- hesperidin
- extracting
- column
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- YRCWQPVGYLYSOX-UHFFFAOYSA-N synephrine Chemical compound CNCC(O)C1=CC=C(O)C=C1 YRCWQPVGYLYSOX-UHFFFAOYSA-N 0.000 title claims abstract description 78
- ARGKVCXINMKCAZ-UHFFFAOYSA-N neohesperidine Natural products C1=C(O)C(OC)=CC=C1C1OC2=CC(OC3C(C(O)C(O)C(CO)O3)OC3C(C(O)C(O)C(C)O3)O)=CC(O)=C2C(=O)C1 ARGKVCXINMKCAZ-UHFFFAOYSA-N 0.000 title claims abstract description 76
- ARGKVCXINMKCAZ-UZRWAPQLSA-N neohesperidin Chemical compound C1=C(O)C(OC)=CC=C1[C@H]1OC2=CC(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O[C@H]3[C@@H]([C@H](O)[C@@H](O)[C@H](C)O3)O)=CC(O)=C2C(=O)C1 ARGKVCXINMKCAZ-UZRWAPQLSA-N 0.000 title claims abstract description 39
- 229960003684 oxedrine Drugs 0.000 title claims abstract description 39
- 239000001100 (2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one Substances 0.000 title claims abstract description 37
- QUQPHWDTPGMPEX-UHFFFAOYSA-N Hesperidine Natural products C1=C(O)C(OC)=CC=C1C1OC2=CC(OC3C(C(O)C(O)C(COC4C(C(O)C(O)C(C)O4)O)O3)O)=CC(O)=C2C(=O)C1 QUQPHWDTPGMPEX-UHFFFAOYSA-N 0.000 title claims abstract description 37
- QUQPHWDTPGMPEX-UTWYECKDSA-N aurantiamarin Natural products COc1ccc(cc1O)[C@H]1CC(=O)c2c(O)cc(O[C@@H]3O[C@H](CO[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O)cc2O1 QUQPHWDTPGMPEX-UTWYECKDSA-N 0.000 title claims abstract description 37
- APSNPMVGBGZYAJ-GLOOOPAXSA-N clematine Natural products COc1cc(ccc1O)[C@@H]2CC(=O)c3c(O)cc(O[C@@H]4O[C@H](CO[C@H]5O[C@@H](C)[C@H](O)[C@@H](O)[C@H]5O)[C@@H](O)[C@H](O)[C@H]4O)cc3O2 APSNPMVGBGZYAJ-GLOOOPAXSA-N 0.000 title claims abstract description 37
- VUYDGVRIQRPHFX-UHFFFAOYSA-N hesperidin Natural products COc1cc(ccc1O)C2CC(=O)c3c(O)cc(OC4OC(COC5OC(O)C(O)C(O)C5O)C(O)C(O)C4O)cc3O2 VUYDGVRIQRPHFX-UHFFFAOYSA-N 0.000 title claims abstract description 37
- QUQPHWDTPGMPEX-QJBIFVCTSA-N hesperidin Chemical compound C1=C(O)C(OC)=CC=C1[C@H]1OC2=CC(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO[C@H]4[C@@H]([C@H](O)[C@@H](O)[C@H](C)O4)O)O3)O)=CC(O)=C2C(=O)C1 QUQPHWDTPGMPEX-QJBIFVCTSA-N 0.000 title claims abstract description 37
- 229940025878 hesperidin Drugs 0.000 title claims abstract description 37
- 238000000034 method Methods 0.000 title claims abstract description 20
- 235000020971 citrus fruits Nutrition 0.000 title abstract description 6
- 241000207199 Citrus Species 0.000 title abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 35
- 239000007788 liquid Substances 0.000 claims abstract description 31
- 239000011347 resin Substances 0.000 claims abstract description 29
- 229920005989 resin Polymers 0.000 claims abstract description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 24
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 22
- 235000011114 ammonium hydroxide Nutrition 0.000 claims abstract description 19
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 19
- 150000001768 cations Chemical class 0.000 claims abstract description 19
- 238000001953 recrystallisation Methods 0.000 claims abstract description 19
- 239000000047 product Substances 0.000 claims abstract description 17
- 238000002425 crystallisation Methods 0.000 claims abstract description 16
- 230000008025 crystallization Effects 0.000 claims abstract description 16
- 238000005406 washing Methods 0.000 claims abstract description 16
- 238000001556 precipitation Methods 0.000 claims abstract description 4
- 230000001105 regulatory effect Effects 0.000 claims abstract 2
- 239000000706 filtrate Substances 0.000 claims description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 22
- 239000012043 crude product Substances 0.000 claims description 19
- 235000013399 edible fruits Nutrition 0.000 claims description 19
- 239000000284 extract Substances 0.000 claims description 19
- 240000004307 Citrus medica Species 0.000 claims description 16
- 238000003756 stirring Methods 0.000 claims description 16
- 230000000694 effects Effects 0.000 claims description 12
- 239000006210 lotion Substances 0.000 claims description 12
- 238000001816 cooling Methods 0.000 claims description 11
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 10
- 239000013078 crystal Substances 0.000 claims description 10
- 230000002378 acidificating effect Effects 0.000 claims description 9
- 238000001914 filtration Methods 0.000 claims description 7
- 238000002203 pretreatment Methods 0.000 claims description 7
- 108010059820 Polygalacturonase Proteins 0.000 claims description 6
- 239000012141 concentrate Substances 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 5
- 239000011780 sodium chloride Substances 0.000 claims description 5
- 241001672694 Citrus reticulata Species 0.000 claims description 4
- 238000002242 deionisation method Methods 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 239000002994 raw material Substances 0.000 claims description 4
- 238000004458 analytical method Methods 0.000 claims description 3
- 230000005089 fruit drop Effects 0.000 claims description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000003463 adsorbent Substances 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 238000010298 pulverizing process Methods 0.000 claims description 2
- 239000003513 alkali Substances 0.000 abstract description 3
- 238000001179 sorption measurement Methods 0.000 abstract description 3
- 235000019441 ethanol Nutrition 0.000 abstract 3
- 238000005325 percolation Methods 0.000 abstract 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 1
- 244000183685 Citrus aurantium Species 0.000 abstract 1
- 235000007716 Citrus aurantium Nutrition 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 239000002244 precipitate Substances 0.000 abstract 1
- 238000000967 suction filtration Methods 0.000 description 13
- 238000000605 extraction Methods 0.000 description 12
- 230000000274 adsorptive effect Effects 0.000 description 5
- 150000002500 ions Chemical class 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 108010093305 exopolygalacturonase Proteins 0.000 description 2
- 229930003944 flavone Natural products 0.000 description 2
- 235000011949 flavones Nutrition 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000002137 ultrasound extraction Methods 0.000 description 2
- 240000002319 Citrus sinensis Species 0.000 description 1
- 235000005976 Citrus sinensis Nutrition 0.000 description 1
- VSRVRBXGIRFARR-CIYSLCTESA-N Neohesperidose Natural products O([C@@H]1[C@@H](O)[C@H](O)[C@H](CO)O[C@H]1O)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](C)O1 VSRVRBXGIRFARR-CIYSLCTESA-N 0.000 description 1
- 238000000944 Soxhlet extraction Methods 0.000 description 1
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 description 1
- 238000003916 acid precipitation Methods 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- VSRVRBXGIRFARR-OUEGHFHCSA-N alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranose Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O VSRVRBXGIRFARR-OUEGHFHCSA-N 0.000 description 1
- 229940088623 biologically active substance Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- -1 flavone compounds Chemical class 0.000 description 1
- 150000002213 flavones Chemical class 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- 150000008131 glucosides Chemical class 0.000 description 1
- AIONOLUJZLIMTK-AWEZNQCLSA-N hesperetin Chemical compound C1=C(O)C(OC)=CC=C1[C@H]1OC2=CC(O)=CC(O)=C2C(=O)C1 AIONOLUJZLIMTK-AWEZNQCLSA-N 0.000 description 1
- 229960001587 hesperetin Drugs 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 239000002893 slag Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Landscapes
- Medicines Containing Plant Substances (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
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CN201510892989.6A CN105399787B (en) | 2015-12-08 | 2015-12-08 | A method of extracting aurantiamarin, neohesperidin and synephrine from orange peel, fruit |
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CN201510892989.6A CN105399787B (en) | 2015-12-08 | 2015-12-08 | A method of extracting aurantiamarin, neohesperidin and synephrine from orange peel, fruit |
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CN105399787A true CN105399787A (en) | 2016-03-16 |
CN105399787B CN105399787B (en) | 2018-11-13 |
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Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106083940A (en) * | 2016-07-11 | 2016-11-09 | 湖南华诚生物资源股份有限公司 | A kind of method extracting high purity novel aurantiamarin from Fructus Aurantii Immaturus |
CN106220698A (en) * | 2016-07-19 | 2016-12-14 | 江西海富生物工程有限公司 | A kind of method of separating high-purity Hesperidin, neohesperidin, naringin and Neosynephrine from Fructus Aurantii Immaturus |
CN107954883A (en) * | 2017-12-05 | 2018-04-24 | 贺州学院 | A kind of method that synephrine is extracted from ripe navel orange pericarp |
CN109796507A (en) * | 2019-02-25 | 2019-05-24 | 涟源康麓生物科技有限公司 | The aurantiamarin remaking the preparation method of aurantiamarin and being prepared |
CN111777653A (en) * | 2020-08-21 | 2020-10-16 | 江西海富生物工程有限公司 | Preparation method of pure natural high-content neohesperidin |
CN112047846A (en) * | 2020-10-13 | 2020-12-08 | 四川大学 | Method for extracting synephrine, naringin and neohesperidin from immature bitter oranges by using ultrasonic-assisted aqueous two-phase system |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101293906A (en) * | 2007-04-25 | 2008-10-29 | 西安皓天生物工程技术有限责任公司 | Method for extracting high purity novel aurantiamarin |
CN101643489A (en) * | 2009-05-26 | 2010-02-10 | 苏州派腾生物医药科技有限公司 | Process for preparing hesperidin |
CN102477056A (en) * | 2010-11-25 | 2012-05-30 | 苏州宝泽堂医药科技有限公司 | Method for purifying neohesperidin |
-
2015
- 2015-12-08 CN CN201510892989.6A patent/CN105399787B/en active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101293906A (en) * | 2007-04-25 | 2008-10-29 | 西安皓天生物工程技术有限责任公司 | Method for extracting high purity novel aurantiamarin |
CN101643489A (en) * | 2009-05-26 | 2010-02-10 | 苏州派腾生物医药科技有限公司 | Process for preparing hesperidin |
CN102477056A (en) * | 2010-11-25 | 2012-05-30 | 苏州宝泽堂医药科技有限公司 | Method for purifying neohesperidin |
Non-Patent Citations (3)
Title |
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于新等: "《天然食品添加剂》", 31 March 2014 * |
廖茂梁等: "树脂分离纯化枳实中辛氟林的工艺研究", 《现代药物与临床》 * |
戴好富等: "《天然产物现代分离技术》", 31 December 2006 * |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106083940A (en) * | 2016-07-11 | 2016-11-09 | 湖南华诚生物资源股份有限公司 | A kind of method extracting high purity novel aurantiamarin from Fructus Aurantii Immaturus |
CN106083940B (en) * | 2016-07-11 | 2019-03-26 | 湖南华诚生物资源股份有限公司 | A method of extracting high purity novel aurantiamarin from the dried immature fruit of citron orange |
CN106220698A (en) * | 2016-07-19 | 2016-12-14 | 江西海富生物工程有限公司 | A kind of method of separating high-purity Hesperidin, neohesperidin, naringin and Neosynephrine from Fructus Aurantii Immaturus |
CN107954883A (en) * | 2017-12-05 | 2018-04-24 | 贺州学院 | A kind of method that synephrine is extracted from ripe navel orange pericarp |
CN109796507A (en) * | 2019-02-25 | 2019-05-24 | 涟源康麓生物科技有限公司 | The aurantiamarin remaking the preparation method of aurantiamarin and being prepared |
CN109796507B (en) * | 2019-02-25 | 2020-12-25 | 涟源康麓生物科技有限公司 | Preparation method of reconstituted hesperidin and hesperidin prepared by preparation method |
CN111777653A (en) * | 2020-08-21 | 2020-10-16 | 江西海富生物工程有限公司 | Preparation method of pure natural high-content neohesperidin |
CN111777653B (en) * | 2020-08-21 | 2023-07-21 | 江西海富生物工程有限公司 | Preparation method of pure natural high-content neohesperidin |
CN112047846A (en) * | 2020-10-13 | 2020-12-08 | 四川大学 | Method for extracting synephrine, naringin and neohesperidin from immature bitter oranges by using ultrasonic-assisted aqueous two-phase system |
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CN105399787B (en) | 2018-11-13 |
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Denomination of invention: A Method for Extracting Hesperidin, Neohesperidin, and Synephrine from Orange Peel and Fruit Effective date of registration: 20231027 Granted publication date: 20181113 Pledgee: Bank of China Limited by Share Ltd. Guilin branch Pledgor: GUILIN SANLENG BIOTECH Co.,Ltd. Registration number: Y2023450000133 |